C-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-methyleneamine → 1-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-ethylamine

HRID 1922216

Reaction equation

HRID 1922216 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]=[NH:12])[C:5]=2[O:4][CH2:3][CH2:2]1.[CH3:13][Mg]Br>C1(C)C=CC=CC=1.C(OCC)C>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]([NH2:12])[CH3:13])[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 86618567C-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-methyleneamineHCID 178418573HCID 178418573, compound

Product 1

HCID 577255011-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-ethylamine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

The dried resin to which the C-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-methyleneamine (1 eq) was bound was suspended in dry toluene. Under a nitrogen atmosphere methyl magnesium bromide (150 eq) in a 3 M solution in ethyl ether was added. This mixture was shaken for 24 hours at 60° C. then filtered and washed with toluene, water, then methanol and dichloromethane alternately three times. The final wash was with methanol. The solid was dried under vacuum.

Workup

  1. filtrationthen filtered
  2. washwashed with toluene, water
  3. washThe final wash
  4. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-d85ab47f3527421590be7e05eaf7e6c8
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Linked notes

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